Experiences Along the Great Chesapeake Bay Loop



Featured Places

Family playing with water cannons
Urban Pirates
Woman laughing on a boat
Boating on the Chesapeake Bay
Photo By: Clark Vandergrift
People riding bicycles
Biking on the Great Chesapeake Bay Loop
With such spectacular sunsets on the beach, you may miss that there's plenty to do in this town's history museums and nature parks. Photo By: Chris Williamson

1 25 Can’t-Miss Things to Do Along the Chesapeake Bay

Play, sight-see, eat, socialize, collect and explore along Maryland’s famous estuary. Use these 25 ideas for things to see and do along the Chesapeake to get you going.

More information...

 National Oyster Shucking Championships Photo By: St Mary's County

2 Things to See and Do in Southern Maryland

In Southern Maryland, history and culture mingle on the shores of the Chesapeake Bay. 

More information...

The National Aquarium in Baltimore Photo By: Visit Baltimore

3 Things to See and Do in Central Maryland

From Annapolis—Maryland’s capital city and the Sailing Capital of the World—to the bustling metropolis of Baltimore, to the Piedmont forests and the shores of the Chesapeake Bay, the Central Region offers thriving cultural destinations, history, music and more.

More information...

Glasses of wine with the Maryland State Flag behind Photo By: The Maryland Wineries Association

4 Things to See and Do on the Eastern Shore

Maryland’s Eastern Shore is home to spectacular sunsets, world-class seafood and produce, nature, history and so much more.

More information...

Guitar building Photo By: Paul Reed Smith Guitars

5 Nifty off 50

U.S. Route 50 is the major east-west route of the U.S. Highway system and it starts and  cuts right through Maryland. Be sure to see the unique places and people along this iconic road.

More information...

This world-class museum houses art from ancient Egypt through the 20th Century. Photo By: Visit Baltimore

6 Art of the Chesapeake

Discover the best galleries and arts events and learn about the unique art of Maryland’s Chesapeake Bay.

More information...

This Chesapeake Bay beach is famous with fossil hunters looking for sharks teeth.

7 National and State Parks

Get in touch with the lives of great Americans like Harriet Tubman, Clara Barton and Thomas Stone. See historic places like Fort McHenry and the Chesapeake and Ohio Canal where the very course of history was changed. Lose yourself in one of a kind landscapes at public parks like Assateague, Sandy Point and Blackwater.

More information...

Enjoy the hands-on exhibits and overnight programs at the lighthouse at this museum.

8 Maryland’s Maritime Museums

Maryland's maritime museums offer so much to explore.  Touch and experience the Chesapeake Bay's marine creatures up-close and discover how they live.  Explore a boat-building workshop and get an insider's look at the life of a waterman.  She how people depend upon a healthy bay.

More information...

9 Tour Maryland’s Lighthouses

Tour these beautiful historic beacons and enjoy the surrounding nature and vistas of the Chesapeake Bay.

More information...

Flowers at Cottage on Smith Island Photo By: Clark Vandergrift, OTD

10 Touring the Islands of Maryland

Maryland is home to hundreds of islands just waiting to be explored. Some are uninhabited or strictly nature preserves, while others are bustling with shops, restaurants and museums.

More information...

women boating Photo By: Clark Vandergrift

11 Boating and Water Sports

Maryland's waterways are a defining feature of the Old Line State, and no visit is complete without leaving the land behind, even for just a little while. 

More information...

travel the crab & oyster trail

12 Maryland Crab & Oyster Trail

Savor the fruits of the Chesapeake Bay on the Maryland Crab & Oyster Trail.

More information...

Purple Wine Photo By: Romano Vineyard

13 Wine Trails Along the Great Chesapeake Bay Loop

Maryland’s distinct microclimates provide diversity and flavor to our wines. Three of the Maryland’s eight wine trails are part of the Great Chesapeake Bay Loop.

Chesapeake Wine Trail, this trail is the perfect excuse to explore the treasures of the Eastern Shore

Legacy Wine Trail,  Southern Maryland's agricultural heritage meets the new legacy of fine wine.

Patuxent Wine Trail, Southern Maryland capitalizes on its Old-World growing traditions to bring an exciting new vision to classic wine profiles.

14 Waterside Events and Festivals

Whether you want to make a splash or just watch, waterside events abound in Maryland.

More information...

Chesapeake Bay Sunset

15 More About the Great Chesapeake Bay Loop

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Travel Around the Chesapeake Bay Loop

Quintessential Chesapeake Bay Towns

Stay Along the Great Chesapeake Bay Loop

Trip Suggestions for the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

Related Articles & Guides


About Authentic

People on a boat crossing the bay to St. Michaels
Trip Suggestions for the Great Chesapeake Bay Loop

With the Great Chesapeake Bay Loop the miles of adventure are unlimited. Explore for a day, escape for a long weekend, or spend a vacation week, or more, enjoying all there is...


Chesapeake Bay Bridge
Great Chesapeake Bay Loop

Plan your Chesapeake Bay adventure


Carroll Wine Trail
Breweries, Wineries and Distilleries

Search our list of Maryland breweries, wineries and distilleries here.


Chesapeake City
Quintessential Chesapeake Bay Towns



Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
Touring the Islands of Maryland

Want to get away to the islands? Maryland is home to hundreds of islands just waiting to be explored! Some are uninhabited or strictly nature preserves, while others are...


Chesapeake Bay Bridge
Travel Around the Great Chesapeake Bay Loop

The elegant, dual spans of Maryland’s Chesapeake Bay Bridge that cross the wide waters of the middle Chesapeake, and the engineering marvel that is the Chesapeake Bay Bridge...